1. Field of the Invention
The present invention relates to porphyrin-phthalocyanine dimer and tetramer having directly-bound π electron systems and a production method thereof.
2. Description of the Related Art
Porphyrins and phthalocyanines, which have a larger molar absorbance coefficient and are superior in photoelectronic properties, have been studied for application as various optical materials. Generally, phthalocyanines have an energy level lower than that of porphyrins, and thus theoretically, it would be possible that energy or electron transfer from porphyrin to phthalocyanine occurs if these compounds are connected to each other. Although there were reports on synthesis and optical properties of such dimers or multimers in which these compounds are connected to each other via one or more atoms, they were still unsatisfactory, in terms of the efficiency in energy or electron transfer (e.g., see the following Non-patent Documents 1 to 8). In addition, there is no report on use of the dimers and others described in these documents as functional terminal molecules, after various kinds of dimer molecules are introduced on the terminal thereof.
The present inventors have developed a method of introducing a variety of functional molecules on the terminal of a multimer having an imidazolyl group-containing porphyrin dimer as its constitutional unit (e.g., see the following Non-patent Document 9 and Patent Document 1). In addition, the present inventors have shown that it is possible to use a porphyrin compound having bisimidazolylporphyrin as its constitutional unit in photoelectric conversion elements (e.g., see the following Non-patent Document 10 and Patent Document 2) and three-dimensional nonlinear optical materials (e.g., see the following Non-patent Document 10 and Patent Document 3), by self-assembly of the compound.
Non-patent document 1: H. Tian, Q. Zhou, S. Shen, H. Xu, J. Photochem. Photobiol. A: Chem. 1993, 72, 163-168.
Non-patent document 2: H. Tian, Q. Zhou, S. Shen, H. Xu, Chin. J. Chem. 1996, 14, 412-420.
Non-patent document 3: X. Li, Q. Zhou, H. Tian, H. Xu, Chin. J. Chem. 1998, 16, 97-108.
Non-patent document 4: L. Li, S. Shen, Q. Yu, Q. Zhou, H. Xu, J. Chem. Soc. Chem. Commun. 1991, 619-620.
Non-patent document 5: S. Gaspard, C. Giannotti, P. Maillard, C. Schaeffer, T. Tran-Thi, J. Chem. Soc. Commun. 1986, 1239-1340.
Non-patent document 6: J. M. Sutton, R. W. Boyle, Chem. Commun. 2001, 2014-2015.
Non-patent document 7: J. Li, J. R. Diers, J. Seth, S. I. Yang, D. F. Bocian, D. Holten, J. S. Lindsey, J. Org. Chem. 1999, 64, 9090-9100.
Non-patent document 8: S. I. Yang, J. Li, H. S. Cho, D. Kim, D. F. Bocian, D. Holten, J. S. Lindsey, J. Mater. Chem. 2000, 10, 283-296.
Non-patent document 9: K. Ogawa and Y. Kobuke, Angew. Chem. Int. Ed. 2000, 39, 4070-4073.
Patent Document 1: Jpn. Pat. Appln. KOKAI Publication No. 2001-213883
Non-patent document 10: (a) A. Nomoto, Y. Kobuke, Chem. Commun. 2002, 1104-1105. (b) A. Nomoto, H. Mitsuoka, H. Ozeki, Y. Kobuke, Chem. Commun. 2003, 1074-1075.
Patent Document 2: Jpn. Pat. Appln. KOKAI Publication No. 2001-253883
Non-patent document 11: K. Ogawa, T. Zhang, K. Yoshihara, and Y. Kobuke, J. Am. Chem. Soc. 2002, 124, 22-23.
Patent Document 3: Jpn. Pat. Appln. KOKAI Publication No. 2003-231688